Diels-Alder Reactions of Vinyl Derivatives of Five-Membered Monoheterocyclic Compounds

Wayland E. Noland, Chang Kiu Lee, Sun Kun Bae, Bong Yul Chung, Chi Sun Hahn, Keun Jae Kim

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Vinylpyrroles having electron-withdrawing substituents react with dienophiles to give [4 + 2] π adducts while the furan and thiophene analogues do not The difference in reactivity among the monoheterocycles can be explained in terms of the greater electron-releasing ability of the nitrogen atom in the pyrrole. The s-cis conformation of the (lif-pyrroi-2-yl)maleate derivatives appears to be an important factor in their undergoing the cycloaddition reaction.

Original languageEnglish (US)
Pages (from-to)2488-2491
Number of pages4
JournalJournal of Organic Chemistry
Volume48
Issue number15
DOIs
StatePublished - Jul 1983

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